The Start of Something New
by PowerfulDeevee
Summary: Gary Oak was a heartbreaker. Countless had loved and lost with him. Will one girl change everything? Full Summary inside. Oldrivalshipping, slight Penguinshipping


Gary Oak was a heartbreaker. Simple. A player. A cheater. Countless people fell in love with him and countless had their hearts broken. Only one girl had never fallen for Gary. Leaf Green. And Gary intended to change that.

Viridian City High School

Leaf's POV

I wandered down the long hallway to my class, my brown hair fell down my back and I used it to hide my face as I wandered down the hallway,

"Gary asked me…"

"Gary is so freaking…"

"I am sure Gary will ask me to…" I sighed. Gary this, Gary that. Gary Oak was our school's heartbreaker. More than half the girls at our school had dated him and had their hearts broken. The other half adored him. I only knew of one other girl that didn't love him and that was Dawn Berlitz. My best friend…

"Hey Greeny. " I looked up to see the devil himself smirking at me. He was cute. I had never denied that. The way his auburn hair fell in his face and his brown eyes burned with a fiery intensity. But he was evil. I smirked.

"Hey Meenie." He cracked a smile at my response.

"They rhyme. Greeny and Meenie." He stepped closer. I stepped back. The hallway was quiet now. Was I about to become a victim of the Oak charm? Maybe I would have if not for Dawn.

"Leaf!" I turned to see my blue haired friend racing towards me. When I turned back to Gary he was glaring at Dawn. He looked like he might punch her. Then a brunette on his left stepped forward.

"That's enough Gary." I recognized the boy. Kenny Clarion. (A/N Random name) He was whom Dawn liked. Gary growled and walked away, leaving Dawn and I puzzled. What had he wanted?

Kenny's House

Kenny's POV

"I almost had her Kenny! I almost had her!" I had been listening to Gary rant for an hour or so. It was all about how he almost had Leaf Green. Almost. Personally, I had no interest in Leaf. Instead I always watched the blue-haired beauty by her side. Dawn Berlitz. Gary, however, was another story. He had liked Leaf ever since we had first met her and Dawn. She, on the other hand, had never liked him. Then she saw the side of him most see, the player side, the cheater side. I was probably the only one who ever saw the nicer side of Gary. I sighed.

"You're never gonna get her Gary. Give up." He whirled around, eyes ablaze.

"I will not give up Kenny! I can't. I don't know why. But I can not let her go." He looked so sad; I was almost tempted to hug him. But then, he would have attacked me so I resisted the urge.

"I don't know Gary. You may have to see what she likes. What she's a sucker for." He glowered.

"Kenny, then she'll know I want her. She can not know that."

"Then you'll have to rely on chance. What she happens to see you doing." Gary sighed dejectedly.

"I guess so. But what are the chances she'll see me doing something nice? One to ten? I only do nice things when I'm alone." I nodded.

"Gary, if she's meant to be with you she will be. We have to wait." I gazed at me doubtfully.

"Alright Kenny. We'll do it your way. But I don't like it."

Was it just me or was he smiling to himself?

Woods outside of Viridian City High School

Dawn's POV

I was more of a shopping girl. Leaf was a nature girl. That was why we were in the middle of the woods after school. Leaf wanted to see the forest.

"Hey Dawn, I think I saw something over there. Be right back." She disappeared. I waited for about ten minutes. Then I noticed a wire running across the clearing I was sitting in. I touched it and BAM! I groaned as I was catapulted over.

"I think I'll call you DeeDee." I whipped around to see Kenny leaning across a tree. I turned bright red as I realized he had been standing there the whole time. My heart started to race, but I crossed my hands over my chest and scowled.

"What for?" Oh my god. My first words to Kenny were 'What for'? Sad.

"Diamond dandruff." He pointed to my hair. My hand flew up.

"Diamond Dandruff? Why…? Oh god!" The blood rushed to my face as I realized my hair was standing straight up and sparkles were coming off it. Kenny smiled. Then his face twisted into confusion.

"Where's Leaf?" I tried to push away my jealousy. Why did Kenny want to know where Leaf was?

"She went into the forest. She saw something." His face broke into a smile.

"Then she'll see Gary helping that bird…" I think I must have misheard that last part. Gary Oak helping someone? Not possible. But my thoughts broke when Kenny grinned at me.

"See ya later DeeDee." I smiled back before the nickname registered.

"Hey! Don't call me DeeDee!" But he was already gone.

Viridian Woods

Gary's POV

I set the baby bird back in the nest. Watching it play with its mother, I felt a rare smile grace my face.

"Wow. You're smiling." I twisted around. Only one girl has a voice like that…

Sure enough Leaf was leaning against a tree. Her hair fell casually against her face as she appraised me. I found myself willing her to approve my. Willing her to except me…

Her eyes flicked to the baby bird and then back to my face. Then she did something I never thought I'd see her do in my presence. She cracked a smile.

"You know, you're not so bad Oak." As she turned to leave she glanced back over her shoulder.

"You should be sweet more often. Less of a bad boy. It makes you more appealing." She disappeared into the trees. I grinned. Then I shouted after her.

"I'll do it more often if you'll go out with me Green!" Her gentle laughter floated back to me.

"Sure. Pick me up at seven. This appears to be the start of something new." I grinned. Funny how much one good deed can change a person's opinion with you. Then what Leaf said registered.

I leapt into the air shoving my fist up.

"Yes!"

**Sorry the ending was kind of rushed. And sorry about the lack of romance and length. It's just supposed to be a short one-shot. R&R!**


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